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JEE Main levelSingle correct optionDifficulty 2 of 3ap084

2-Methyl-3-phenylbutane-2,3-diol, , is heated with dilute . The product is

  1. A2-methyl-3-phenylbut-3-en-2-ol
  2. B2,2-dimethyl-1-phenylpropan-1-one
  3. C3-methyl-2-phenylbutanal
  4. D3-methyl-3-phenylbutan-2-one

Answer: D

The benzylic tertiary cation is the more stable one. A methyl shift from the neighbouring gives . If the other cation formed, phenyl migration would give the same ketone, so 3-methyl-3-phenylbutan-2-one is obtained either way.
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